Fragmentation of the (R)-(+)-1-phenyl-1-propanol radical cation ([(BZC 2H5)R]+) is markedly affected by asymmetric microsolvation (see picture). The Cα-C β bond cleavage in the heterochiral [ (BZC2H 5)R.BDSS]+ cluster is more efficient than in the homochiral [(BZC2H5) R.BDRR]+. The difference is ascribed to structural factors that make BDSS a better H-bond acceptor than BDRR in their adducts with [(BZC2H5) R]+. BZ = PhCHOH, BD = 2,3-butanediol.

Catone, D., Guidoni, A.G., Paladini, A., Piccirillo, S., Rondino, F., Satta, M., et al. (2004). Homolytic C-alpha-C-beta bond cleavage in a chiral alkylarene radical cation: Effects of asymmetric microsolvation. ANGEWANDTE CHEMIE. INTERNATIONAL EDITION, 43(14), 1868-1871 [10.1002/anie.200353462].

Homolytic C-alpha-C-beta bond cleavage in a chiral alkylarene radical cation: Effects of asymmetric microsolvation

PICCIRILLO, SUSANNA;
2004-03-26

Abstract

Fragmentation of the (R)-(+)-1-phenyl-1-propanol radical cation ([(BZC 2H5)R]+) is markedly affected by asymmetric microsolvation (see picture). The Cα-C β bond cleavage in the heterochiral [ (BZC2H 5)R.BDSS]+ cluster is more efficient than in the homochiral [(BZC2H5) R.BDRR]+. The difference is ascribed to structural factors that make BDSS a better H-bond acceptor than BDRR in their adducts with [(BZC2H5) R]+. BZ = PhCHOH, BD = 2,3-butanediol.
Pubblicato
Rilevanza internazionale
Articolo
Sì, ma tipo non specificato
Settore CHIM/03 - Chimica Generale e Inorganica
English
Con Impact Factor ISI
Asymmetric microsolvation; Cluster compounds; Enantioselectivity; Photoelectron spectroscopy; Radical reactions
Carbon; Positive ions; Solvents; Bond cleavage; Fragmentation; Chemical bonds; alkyl group; butanediol; cation; phenyl group; propanol; radical; article; chemical bond; chirality; hydrogen bond; solvation
http://onlinelibrary.wiley.com/doi/10.1002/anie.200353462/pdf
Catone, D., Guidoni, A.G., Paladini, A., Piccirillo, S., Rondino, F., Satta, M., et al. (2004). Homolytic C-alpha-C-beta bond cleavage in a chiral alkylarene radical cation: Effects of asymmetric microsolvation. ANGEWANDTE CHEMIE. INTERNATIONAL EDITION, 43(14), 1868-1871 [10.1002/anie.200353462].
Catone, D; Guidoni, A; Paladini, A; Piccirillo, S; Rondino, F; Satta, M; Scuderi, D; Speranza, M
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2108/57185
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